FR2528029A1 - Detection and removal of phosphate from blood etc. - using emulsions contg. quaternary di:ammonium cpds. - Google Patents

Detection and removal of phosphate from blood etc. - using emulsions contg. quaternary di:ammonium cpds. Download PDF

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FR2528029A1
FR2528029A1 FR8209597A FR8209597A FR2528029A1 FR 2528029 A1 FR2528029 A1 FR 2528029A1 FR 8209597 A FR8209597 A FR 8209597A FR 8209597 A FR8209597 A FR 8209597A FR 2528029 A1 FR2528029 A1 FR 2528029A1
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phosphate ions
phosphate
lipophilic compound
detection
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FR2528029B1 (en
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Association pour la Recherche et le Developpement des Methodes et Processus Industriels
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    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D61/00—Processes of separation using semi-permeable membranes, e.g. dialysis, osmosis or ultrafiltration; Apparatus, accessories or auxiliary operations specially adapted therefor
    • B01D61/38—Liquid-membrane separation
    • B01D61/40—Liquid-membrane separation using emulsion-type membranes
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
    • C01B25/00—Phosphorus; Compounds thereof
    • C01B25/16—Oxyacids of phosphorus; Salts thereof
    • C01B25/26—Phosphates
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
    • C01B25/00—Phosphorus; Compounds thereof
    • C01B25/16—Oxyacids of phosphorus; Salts thereof
    • C01B25/26—Phosphates
    • C01B25/30—Alkali metal phosphates
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N27/00—Investigating or analysing materials by the use of electric, electrochemical, or magnetic means
    • G01N27/26—Investigating or analysing materials by the use of electric, electrochemical, or magnetic means by investigating electrochemical variables; by using electrolysis or electrophoresis
    • G01N27/28—Electrolytic cell components
    • G01N27/30—Electrodes, e.g. test electrodes; Half-cells
    • G01N27/333—Ion-selective electrodes or membranes
    • G01N27/3335—Ion-selective electrodes or membranes the membrane containing at least one organic component

Abstract

A lipophilic compound having two quaternary ammonium groups that form labile complexes with phosphate ions, that is dissolved in an organic phase, is contacted with an aq. soln. contg. phosphate ions, for their detection, extraction, or selective removal. The quaternary ammonium cpds. are pref. of formulae (I), (II) or (III) (where R1-R7 is aliphatic groups). Contact between the ammonium cpd. and the aq. soln. of phosphate ions is achieved by preparing a water-in-oil emulsion with the organic soln. as the continuous phase. The phosphate ions are usually contained in blood and the process is used to remove them in cases of renal insufficiency.

Description

La régulation de la concentration en phosphate dans le sang est un des problèmes auxquels sont confrontés les néphrologues au cours du traitement de 'insuffisance rénale. L'élimination des ions phosphate en excès se fait actuel liement au cours des seances de dialyse d'une part, et par ingestion de chélatants (gels d'hydroxyde d'aluminium) entre les séances de dialyse d'autre part. The regulation of phosphate concentration in the blood is one of the problems faced by nephrologists during the treatment of renal failure. The removal of excess phosphate ions is presently occurring during dialysis sessions on the one hand, and by ingestion of chelants (aluminum hydroxide gels) between dialysis sessions on the other hand.

La consommation de ces derniers produits pourrait, à la longue, provoquer l'accumulation d'aluminium dans le cerveau. Un produit de remplacement serait souhaitable. The consumption of these products could, in the long run, cause the accumulation of aluminum in the brain. A replacement product would be desirable.

La régénération des bains de dialyse, par utilisation de systèmes -r-- caces piégeant les produits toxiques extraits du sang, est une condition préalable à la réalisation de reins artificiels miniaturisés, voire portables. Ces systèmes, devraient, entre autre, permettre l'élimination des phosphates. The regeneration of the dialysis baths, by using -r-- cient systems trapping the toxic products extracted from the blood, is a prerequisite for the realization of artificial kidneys miniaturized, even portable. These systems should, among other things, allow the elimination of phosphates.

L'utilisation d'émulsions de type eau-dans-huile peut être envisagée pour la régénération des bains de dialyse ou le piégeage in vivo des toxiques. The use of water-in-oil emulsions can be envisaged for the regeneration of dialysis baths or the in vivo trapping of toxics.

Dispersées dans le milieu biologique à traiter, ces émulsions possédent une phase continue organique formant une membrane liquide entre deux phases aqueuses et au travers de laquelle peuvent s'effectuer des transferts de matière. Les toxiques, après diffusion dans la membrane, sont stockés ou détruits par réaction chimique dans la phase aqueuse dispersée de' l'émulsion. Pour augmenter l'efficacité et la sélectivité de ces transferts, on utilise des porteurs, molécules lipophiles capables de se complexer de manière sélective et reversi hie avec un produit toxique donné.Dispersed in the biological medium to be treated, these emulsions have an organic continuous phase forming a liquid membrane between two aqueous phases and through which material transfers can take place. The toxins, after diffusion into the membrane, are stored or destroyed by chemical reaction in the dispersed aqueous phase of the emulsion. To increase the efficiency and selectivity of these transfers, carriers are used which are lipophilic molecules capable of complexing selectively and reversing with a given toxic product.

Dans le cas de l'élimination des anions phosphate , on peut utiliser des porteurs chargés positivement qui forment un "complexe" neutre, soluble dans la membrane liquide. Ces porteurs doivent se montrer particulièrement sélectifs vis-a-vis des ions chlorure, au moins 20 fois plus concentrés que les ions phosphate dans les liquides biologiques. In the case of the removal of phosphate anions, positively charged carriers can be used which form a neutral "complex", soluble in the liquid membrane. These carriers must be particularly selective for chloride ions, at least 20 times more concentrated than phosphate ions in body fluids.

Nous avons trouvé que certains composés lipophiles possédant deux fonctions "ammonium quaternaire" pouvaient permettre un transport sélectif et efficace $!ins phosphate en milieu chlorure. Ces composés ont des formules chimiques représentées sur la figure 1, ou les groupes notés R représentent des faines carbonées. We have found that certain lipophilic compounds having two "quaternary ammonium" functions may allow selective and efficient transport of phosphate in a chloride medium. These compounds have chemical formulas shown in FIG. 1, or the groups marked R represent carbonaceous liners.

Des exemples typiques des résultats obtenus sont décrits ci-dessous. Typical examples of the results obtained are described below.

Dans un réacteur agité, on pince 70 mi d'une solution de NaCi (0,1 mole/l) et de K2NP04 ( 5 . 10 mole/l). On disperse 20 g d'une émulsion au moyen d'un agitateur magnétique tournant à 500 tours/mn. On suit ltevolution de la concentration en ions phosphate par dosages colorimétriques d'échantillons et celle des iots chlorure par argentimétrie.  In a stirred reactor, 70 ml of a solution of NaCl (0.1 mol / l) and K 2 NPO 4 (5 × 10 mol / l) were clamped. 20 g of an emulsion are dispersed by means of a magnetic stirrer rotating at 500 revolutions / min. The evolution of the phosphate ion concentration is monitored by colorimetric assays of the samples and that of the chloride ions by argentiometry.

Essai n 1
Emulsion (pourcentage en poids):
* Montanide 80 .......................................... 4,99% * N,N (di-méthyl, héxadécyl) éthylène di-ammonium, bromure 0,09 % * Paraffine fluide ..........................................54,82% * Octanol ................................ 6,67 % * Solution molaire d'acétate de calcium ..................... 33,44%
Cinétique de transfert:

Figure img00020001
Test No. 1
Emulsion (percentage by weight):
* Montanide 80 .......................................... 4.99% * N, N (di-methyl, hexadecyl) ethylene di-ammonium, bromide 0.09% * Fluid paraffin ........................... ............... 54,82% * Octanol ............................. ... 6.67% * Molar solution of calcium acetate ..................... 33,44%
Transfer kinetics:
Figure img00020001

<tb> Concentrations <SEP> (mole/l) <SEP> phosphate <SEP> chlorure
<tb> temps(mn)
<tb> <SEP> 0 <SEP> 5,0 <SEP> . <SEP> 10-3 <SEP> 0,114
<tb> <SEP> 31 <SEP> 4,58 <SEP> . <SEP> 10-3 <SEP>
<tb> <SEP> 60 <SEP> - <SEP> 0,120
<tb> <SEP> 90 <SEP> 3,18 <SEP> . <SEP> 10-3 <SEP> 0,114
<tb> <SEP> 120 <SEP> 2,92 <SEP> . <SEP> 10-3 <SEP> 0,107
<tb> <SEP> 180 <SEP> 2,70 <SEP> .<SEP> 10-3 <SEP> 0,105
<tb>
Essai n 2
Emulsion (pourcentage en poids):
* Montanide 80............................................. 5,01%
* N,N (Méthyl, dodécyl) pipérazinium, chlorure............. 0,06%
* Octanol.................................................. 6,74% * Paraffine fluide .......... 54,89 % * Solution molaire d'acétate de calcium...................... 32,43% cinétique de transfert:

Figure img00020002
<tb> Concentrations <SEP> (mole / l) <SEP> phosphate <SEP> chloride
<tb> time (mn)
<tb><SEP> 0 <SEP> 5.0 <SEP>. <SEP> 10-3 <SEP> 0.114
<tb><SEP> 31 <SEP> 4.58 <SEP>. <SEP> 10-3 <SEP>
<tb><SEP> 60 <SEP> - <SEP> 0.120
<tb><SEP> 90 <SEP> 3,18 <SEP>. <SEP> 10-3 <SEP> 0.114
<tb><SEP> 120 <SEP> 2.92 <SEP>. <SEP> 10-3 <SEP> 0.107
<tb><SEP> 180 <SEP> 2.70 <SEP>. <SEP> 10-3 <SEP> 0.105
<Tb>
Test 2
Emulsion (percentage by weight):
* Montanide 80 ............................................. 5, 01%
* N, N (methyl, dodecyl) piperazinium, chloride ............. 0.06%
* Octanol ................................................ .. 6,74% * Fluid Paraffin .......... 54,89% * Molar solution of calcium acetate ................... ... 32.43% kinetics of transfer:
Figure img00020002

<tb> <SEP> temps <SEP> (mn) <SEP> concentration <SEP> en <SEP> phosphate <SEP> (mole/l)
<tb> <SEP> 0 <SEP> - <SEP> 5,0 <SEP> . <SEP> 10-3 <SEP>
<tb> <SEP> 30 <SEP> 2,99 <SEP> . <SEP> 10-3
<tb> <SEP> 60 <SEP> 2,30 <SEP> .<SEP> ions <SEP>
<tb> 120 <SEP> 1,46
<tb>
Concentration en chlorure : constante (O,11 mole/I)
Essai n 3
Emulsion (pourcentage en poids): * Montanide 80................................... 5,74% c N,N.(di-méthyl hexadecyl) N - méthyl, éthylène triamine,
di-bromure 0,08 % * Octanol........................................ 6,65% * Paraffine fluide............................... 54,11% s Solution molaire d'acétate de calcium 33,41%
Cinétique de transfert:

Figure img00030001
<tb><SEP> time <SEP> (min) <SEP> concentration <SEP> in <SEP> phosphate <SEP> (mole / l)
<tb><SEP> 0 <SEP> - <SEP> 5.0 <SEP>. <SEP> 10-3 <SEP>
<tb><SEP> 30 <SEP> 2.99 <SEP>. <SEP> 10-3
<tb><SEP> 60 <SEP> 2.30 <SEP>. <SEP> ions <SEP>
<tb> 120 <SEP> 1.46
<Tb>
Chloride concentration: constant (0.1 mol / I)
Test 3
Emulsion (percentage by weight): * Montanide 80 ................................... 5,74% c N, N- (dimethyl hexadecyl) N-methyl, ethylene triamine,
di-bromide 0.08% * Octanol ........................................ 6 , 65% * Fluid paraffin ............................... 54.11% s Molar solution of calcium acetate 33 , 41%
Transfer kinetics:
Figure img00030001

<tb> <SEP> Concentrations <SEP> (mole/l)
<tb> temps <SEP> (mn) <SEP> phosphate <SEP> chlorure
<tb> <SEP> O <SEP> 5,00 <SEP> . <SEP> 10-3 <SEP> 0,117
<tb> <SEP> 30 <SEP> 4,14.10-3 <SEP>
<tb> <SEP> 45 <SEP> 3,90.10-3 <SEP>
<tb> <SEP> 90 <SEP> 2,78.10-3 <SEP>
<tb> <SEP> 120 <SEP> 2,31.10-3 <SEP> 0,117
<tb> <SEP> 180 <SEP> 1,46 <SEP> . <SEP> 10-3 <SEP> 0,116
<tb> <tb><SEP> Concentrations <SEP> (mole / l)
<tb> time <SEP> (min) <SEP> phosphate <SEP> chloride
<tb><SEP> O <SEP> 5.00 <SEP>. <SEP> 10-3 <SEP> 0.117
<tb><SEP> 30 <SEP> 4,14.10-3 <SEP>
<tb><SEP> 45 <SEP> 3,90.10-3 <SEP>
<tb><SEP> 90 <SEP> 2.78.10-3 <SEP>
<tb><SEP> 120 <SEQ> 2.31.10-3 <SEP> 0.117
<tb><SEP> 180 <SEP> 1.46 <SEP>. <SEP> 10-3 <SEP> 0.116
<Tb>

Claims (6)

REVENDICATIONS 1. Utilisation dans un procédé pour la détection, l'.xtraction-ou le transport sélectif d'ions phosphate contenus dans une solution aqueuse,d'un composé lipophile possédant deux fonctions "ammonium quaternaire", susceptible de former des complexes labiles avec les ions phosphate, et dissout dans une phase organique mise en contact avec la dite solution aqueuse. 1. Use in a process for the detection, extraction or selective transport of phosphate ions contained in an aqueous solution, of a lipophilic compound having two "quaternary ammonium" functions, capable of forming labile complexes with the phosphate ions, and dissolved in an organic phase brought into contact with said aqueous solution. 2. Procédé selon la revendication I dans lequel le composé lipoulllie est un dérivé de l'éthylène -di-amine. 2. The process of claim 1 wherein the lipophilic compound is a derivative of ethylene-di-amine. 3. Procédé selon la revendication 1 dans lequel le composé lipophile est un dérivé de l'éthylène -tri-amine. 3. The process of claim 1 wherein the lipophilic compound is an ethylene tri-amine derivative. 4. Procédé selon la revendication 1 dans lequel le composé lipophile est un dérivé de la pipérazine. The process of claim 1 wherein the lipophilic compound is a piperazine derivative. 5. Procédé selon l'une des revendications là 4, permettant l'élimina- tion des ions phosphate contenus dans un liquide biologique à une concentration anormalement élevée, caractérisé par le fait que la membrane organique dans laquelle est dissout le dit composé lipophile constitue la phase continue d'une émulsion de type eau-dans-huile. 5. Method according to one of claims 4, for the elimination of the phosphate ions contained in a biological fluid at an abnormally high concentration, characterized in that the organic membrane in which said lipophilic compound is dissolved constitutes the continuous phase of a water-in-oil type emulsion. 6. Procédé selon l'une des revendications 1 à 4, utilisé pour le dosage des ions phosphate, dans lequel la membrane contenant le complexant lipophile des ions phosphate constitue la partie sensible d'une électrode de mesure.  6. Method according to one of claims 1 to 4, used for the determination of phosphate ions, wherein the membrane containing the lipophilic complexing agent of the phosphate ions constitutes the sensitive part of a measuring electrode.
FR8209597A 1982-06-02 1982-06-02 Detection and removal of phosphate from blood etc. - using emulsions contg. quaternary di:ammonium cpds. Granted FR2528029A1 (en)

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FR2528029B1 FR2528029B1 (en) 1986-01-24

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0568968A2 (en) * 1992-05-08 1993-11-10 Teijin Limited Blood-treating device, and process for producing the same
CN104390961A (en) * 2014-11-11 2015-03-04 中国矿业大学 Color developing method of hydrogen-containing phosphinate
JP2017052751A (en) * 2015-09-09 2017-03-16 東ソー株式会社 Gemini type surfactant

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2013523A (en) * 1978-02-01 1979-08-15 Exxon Research Engineering Co Blood dialysis processes and apparatus using stabilized liquid membrane capsules
US4183918A (en) * 1977-03-08 1980-01-15 Exxon Research & Engineering Co. Detoxifying-medicinal emulsions

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4183918A (en) * 1977-03-08 1980-01-15 Exxon Research & Engineering Co. Detoxifying-medicinal emulsions
GB2013523A (en) * 1978-02-01 1979-08-15 Exxon Research Engineering Co Blood dialysis processes and apparatus using stabilized liquid membrane capsules

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
CHEMIE-INGENIEUR-TECHNIK, volume 52, mai 1980 (WEINHEIM, DE) R. MARR et al. "Fl}ssigmembran-Technik - ]bersicht }ber Ph{nomene, Transportmechanismen und Modellbildungen", pages 399-410 *
CHEMISTRY AND INDUSTRY, no. 19, octobre 1981 (LONDRES, GB) S.S. DAVIS "Liquid membranes and multiple emulsions", pages 683-687 *
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY *
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, volume 102, 27 février 1980, I. TABUSHI et al. "Carrier-mediated selective transport of nucleotides through a liquid membrane", pages 1744-1745 *

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0568968A2 (en) * 1992-05-08 1993-11-10 Teijin Limited Blood-treating device, and process for producing the same
EP0568968A3 (en) * 1992-05-08 1994-02-23 Teijin Ltd
US5486606A (en) * 1992-05-08 1996-01-23 Teijin Limited Cellulosic polymer, blood-treating device, and process for producing the same
CN104390961A (en) * 2014-11-11 2015-03-04 中国矿业大学 Color developing method of hydrogen-containing phosphinate
CN104390961B (en) * 2014-11-11 2016-10-12 中国矿业大学 A kind of coloration method of hydrogeneous phosphinate
JP2017052751A (en) * 2015-09-09 2017-03-16 東ソー株式会社 Gemini type surfactant

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